Triethylamine → HCID 68431569, compound

HRID 1186938Notes

Reaction equation

HRID 1186938 reaction equation
Br[C:2]1[C:11]([CH3:12])=[CH:10][C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[C:3]=1[CH3:13].[CH2:14](N(CC)CC)[CH3:15]>CCO.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:14]([C:2]1[C:11]([CH3:12])=[CH:10][C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[C:3]=1[CH3:13])=[CH2:15]

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 66643825HCID 66643825, compound

Product 1

HCID 68431569HCID 68431569, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

5-Bromo-4,6-dimethyl-2-benzofuran-1(3H)-one (375 mg, 1.56 mmol), potassium vinyl trifluoroborate (417 mg, 3.11 mmol), Pd(dppf)Cl2 (127 mg, 0.156 mmol), and triethylamine (409 μL, 3.11 mmol) were combined together in EtOH (10 mL) and heated at 140° C. for 30 min. Analysis by LC as well as TLC (hexanes/EtOAc=1/0.3) indicated that reaction had gone to completion. The reaction mixture was then diluted with EtOAc, washed with NaCl, dried over Na2SO4, filtered, and concentrated to dryness. The resulting residue was then re-dissolved in dichloromethane, absorbed to silica gel, concentrated, and loaded onto a silica MPLC column for separation to afford of 5-ethenyl-4,6-dimethyl-2-benzofuran-1(3H)-one.

Workup

  1. washwashed with NaCl
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. dissolutionThe resulting residue was then re-dissolved in dichloromethane
  6. customabsorbed to silica gel
  7. concentrationconcentrated
  8. customloaded onto a silica MPLC column for separation

Sources & evidence

ORD record
ord-eb537802e53c404fb4d63f40233e945b
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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